


Matchmaker Charlie

by pherryt



Category: Supernatural
Genre: Angst, Broken Heart, Cat, F/F, F/M, First Kisses, Fluff, M/M, Matchmaking, Multiple Couples, New Neighbor, Oblivious, Other, Pining, Polyamory, Proposals, Revelations, Reverse Prompt Challenge, Reverse Prompt Challenge #2, Reverse Prompt Challenge #2 - Changing Seasons, game nights, happy endings, multiple oblivious people, self sacrificing cas
Language: English
Status: Completed
Published: 2019-02-18
Updated: 2019-02-18
Packaged: 2019-10-30 16:35:28
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,727
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17832188
Author URL: https://archiveofourown.org/users/pherryt/pseuds/pherryt
Summary: After Gilda moves out, leaving Charlie with a broken, pining heart, she's resolved that the best way to deal with it is to make sure everyoneelseis happy.Some folks are already on track with that, but a few more folks need a little nudge, here and there.  Over the course of the year, Charlie spends game nights matchmaking for everyone but herself... but her own happiness is closer than she thinks.





	Matchmaker Charlie

**Author's Note:**

> Alternative title: Winter, Spring Summer and Fall! (Which I can NOT say without singing)
> 
> Written for [ the Reverse Prompts 2nd Challenge](https://reverseprompts.tumblr.com/post/182665595652/reverseprompts-reverse-prompt-challenge-2) Changing Seasons (art by Dmsilvisart)
> 
> Picture Prompt (if you can't see it):  
> Collage of landscape through all four seasons overlaid with a Calico Cat, To Rent sign, Comics, and a card that says "Hope your day is as nice as your butt"  
> Took some liberties with the interpretation of a couple of those (We never see the to rent sign but there are two instances that it can be applied to, and comics, well, charlie's a geek, so you know there in there....)

 

It was cold outside, spring just starting to peek through the dismal gray outside, but Charlie only wore jeans and her Harry Potter t-shirt as she danced around her apartment barefoot, getting ready for game night.

She paused, hands on her hips, surveying her handiwork.

The apartment was small, but big enough for the crew she hosted weekly. Counting herself, there were sometimes upwards of 10 folks who gathered for Sunday Night Games.  Normally, there’d be an eleventh, but Gilda had abruptly moved out, leaving Charlie with an empty room, and a broken heart.

Not that they’d even been together, or anything, but Charlie _might_ have been pining after Gilda since almost the second they’d moved in together. But they’d never actually been anything more than just friends and Charlie just had to move on.

She was really looking forward to some lighthearted fun to take her mind off things. And maybe after game night, some of the guys could stick around and commiserate with her.

Thankfully, she had a dining room set that could easily seat 10 if she shoved the couch out of the way first and then set the leaf inside. A bookcase just inside the door held her prized collections of books and games and other various knick knacks. The table already held snack bowls and she’d made sure to stock up on various sodas and energy drinks that morning.

Other than simple cleaning, game night was fairly easy to prep for.

That and corralling Mister Picklebottom. The calico cat had, for some reason, a great fear of some of her guests, and if she felt cornered, the cat would strike and Mister Picklebottom did not hold back her punches. Or scratches. Whatever.

Charlie frowned.

There was no sign of the oddly named cat. Calling out to her, Charlie wandered through the apartment, even forcing herself to check the empty room Gilda had left behind. Nope. Still empty. The further she explored, the more worried she became.

A knock on the door interrupted the search and forcing herself to pause, Charlie hurried over to it, opening it with quick glances to each side to make sure there was no cat suddenly angling to leave the apartment –

But there wasn’t, because when Charlie finally looked up, she was face to face with Mister Picklebottom herself and an unfamiliar, dark haired woman who held the calico cat in her arms.

“Mister Picklebottom! You naughty little thing, you! How did you get out?” Charlie gushed, reaching eagerly for her cat. She cooed over Mister Picklebottom who purred and rubbed her face on Charlie’s before Charlie remembered herself and looked back at the woman who’d returned her.

“Thank you  _so_ much! I was just going crazy looking for Mister Picklebottom!”

The woman startled, her eyes going wide as she looked from between Charlie and the cat and back again. Hesitantly, she spoke. “You are aware this cat is female, right?”

“Yes, she is! But don’t worry, she’s fixed. Despite current appearances, I am  _not_ an irresponsible cat owner,” Charlie assured the woman.

“That’s all right. I have a cat myself, they are masters of getting in and out of anything you don’t want them being able to get in or out of,” the woman said. “I must have misheard this cutie’s name.”

“Oh!” Charlie laughed. “No, you didn’t. I got her from the shelter. Her previous owner had been a child, and I hadn’t the heart to change it.”

“Hence the ridiculous and incorrect name,” Eileen said with a smile. “She’s really very sweet.”

Charlie smiled down at her cat and rubbed her face against Mister Picklebottoms as she spoke. “Yes, yes she is! Such a sweet little monster cat that likes everyone except Benny. Isn’t that right you silly little thing?”

“I’m sorry, what?”

Blinking, Charlie looked up. “What?”

“I didn’t hear what you said, I’m deaf,” the woman said.

“Oh! I’m so sorry, I didn’t…” Charlie juggled the cat, trying to keep a firm grip while still freeing a hand. “I know a little bit of sign language… If you’ll just forgive, I’m a bit rusty…”

“It’s all right, thank you,” the woman said.

“Hey, my name’s Charlie,” Charlie said, beaming, an idea forming in her mind.

“I’m Eileen. It’s nice to meet you, Charlie. I’m new here so I don’t know anyone yet,” Eileen explained.

“Oh hey, I can help with that. Got any plans right now?”

* * *

*#*#*#*#*#*#*#*#*#*#

* * *

After discussing the evenings plans with her new neighbor – literally, the apartment just next door to Charlies - Charlie was happy to hear Eileen accept the offer. Leaving to take care of a few things first, Eileen promised to come back in an hour, when everything should – theoretically, if no one was late – start.

In the meantime, she had Mister Picklebottom to take care of.

Confining the cat to her bedroom was a wrench, hating to curtail the calico’s freedom, but it was the least likely place for the kitty to be disturbed with the comings and goings and opening of doors with all the guests.

She really wished she could get Mister Picklebottom to like Benny. He was like a great big, cuddly Teddy Bear! How could you _not_ like him?

Even Castiel liked him, and considering that Cas had the mother of all crushes on Dean Winchester, who he’d known longer than Benny had and was currently _with_ Benny, that had to be saying something.

Maybe it was her own recently broken heart, but the idea that any of her friends were alone and possibly miserable about being that way had tears forming in her eyes. She wiped them away firmly.

No. She was going to have a good time tonight.

And maybe set a few folks up while she was at it. That would cure a broken heart, right?

Soon enough, people started arriving. Dean and Benny were early, bringing several boxes of pizza along with them. Perfect. Jesse and Cesar came after and then one by one, the rest arrived. Nearly everyone had gotten there by the time Charlies new neighbor made good on her promise.

Answering the door, she greeted Eileen with a beaming smile and a signed word.

“Thank you, Charlie,” Eileen said softly, signing back.

“Well, c’mon in, the gang’s mostly here!” Charlie said enthusiastically, pulling Eileen inside and shutting the door behind them. They turned to the room which had gone mostly quiet at Eileen’s appearance with curiosity. Eileen blushed at being the center of everyone’s attention and Charlie looped an arm around her shoulder and gave her a small, reassuring squeeze.

 “Hey everyone, I’d like you to meet Eileen. She’s new in the building, so I thought I’d introduce her around,” Charlie said, escorting Eileen inside. Charlie beamed as she watched Sam’s eyes catch on Eileen. He had a thing for girls with long, dark hair, even more of a thing if they were smart and strong willed.

At least, if Ruby, Madison and Amelia were anything to go by. Jess was before Charlie’s time, but from what Dean had mentioned once, she was the outlier, being blonde, but had been just as smart and strong as the rest.

Charlie approved.

At any rate, as Sam continued to stare at their new guest, Charlie had a feeling she’d just found herself a match and she prepared settled in to watch the love birds dance around each other. But first, the rest of the introductions.

Turning to face Eileen so the other woman could read Charlie’s lips, she went around the table and pointed. “That’s Dean and his husband Benny. Dean’s brother Sam, their sister Jo. That’s Cas, that’s Garth and those are Jesse and his husband Cesar. Sometimes we have other people here too, but this is the core group.”

“It’s very nice to meet you all,” Eileen said, signing at the same time. She’d explained to Charlie that she didn’t expect everyone to know sign language and she was glad and lucky she spoke well enough to make do if they didn’t. But it was much easier for her if they did.

Charlie could understand that and she made a note to herself to brush up on her own sign language.

Sam and Jo made room for Eileen and quicker than Charlie could have imagined, Eileen fell into place in the group. Charlie watched Sam fumble to sign to Eileen who smiled happily at the effort and soon enough, game night was being interspersed with signing lessons.

Castiel, Charlie wasn’t surprised to note, was actually already fluent and assisted when needed.

In fact, the night went so well, that it wasn’t until people started to disperse that the reality of her situation hit Charlie over the head again.

Feeling suddenly bereft and alone even though there were still folks who hadn’t yet left, Charlie dithered about who to try and pull aside to keep her company a little longer. Garth was eager to get home to Bess who hadn’t come this time. Jesse and Cesar were already gone, Sam was walking Eileen to the door, his coat already in hand. Dean and Benny hadn’t been able to keep their hands off each other all night and looked like they were eager to get going…

Which left Jo and Cas. Jo, who was already clearing away the table and Cas who was staring after Dean and Benny wistfully before shaking his head to help her.

Biting her lip, suddenly decided, Charlie joined Jo and Cas in the kitchen.

“Hey uh, I was wondering if you two might hang around a little longer? Just… maybe a movie or whatever? I have ice cream,” Charlie blurted, then winced. How much more obvious could she be.

Jo and Cas exchanged looks. Jo nodded and Cas said, “Of course, Charlie, whatever you need.”

“I mean, I’m fine, I’m good, don’t get me wrong,” she babbled. “I just… uh… thought since you guys like Mister Picklebottom so much and she can’t come out when Benny’s around…”

“It’s okay, Charlie. We’ve  _all_ been there,” Jo said, clapping a hand on Charlies shoulder.

* * *

*#*#*#*#*#*#*#*#*

* * *

Next Sunday game, Eileen was there first, bringing a casserole with. Everyone had opted for potluck this time around and Charlie had quickly got in contact with Eileen to warn her.

They chattered, Charlie using her broken signs as they puttered about the kitchen. She had homemade garlic bread in the oven and the apartment smelled heavenly.

“Charlie, before the others get here, may I ask you something?” Eileen signed.

“Sure, anything you want.”

“It’s about Cas…”

Charlie’s heart sank. Oh no, she’d thought Eileen and Sam had been getting along so well. How did she explain that Eileen was barking up the wrong tree with Cas?

“Uh… okay? What about Cas?” she asked cautiously.

“Well,” Eileen paused as if she wasn’t sure how to ask what she wanted to ask. “Never mind. It’s prying and none of my business.”

Now okay, if that didn’t get Charlie’s curiosity to ratchet up. She  _had_ to know what was eating Eileen  _now._

“No, no, go ahead. It’s just us girls here…” Charlie said, looking around the room conspiratorially in a thoroughly exaggerated manner though, as she had said, they were the only two there.

Unless you counted her sweet little calico sitting at her feet and staring up with begging eyes.

Eileen laughed at her ridiculousness and nodded, taking her invitation to speak freely with a suddenly sober, but utterly confused look. “I know you said Dean and Benny were together but… you understand, I pick up body language cues easier than most folks?”

Charlie nodded. “Sure, that makes sense.”

“I’m pretty sure all three of them love each other, but Cas is miserable. Did something happen?”

Hand fluttering to her mouth, Charlie made a strangled sound and Eileen looked at her in alarm at whatever face she must be making.

Striving to gain control of her breathing and not shout loud enough for the rest of the building to hear, Charlie bounced on her heals and flapped her hands before finally settling again and grabbing Eileen into a hug.

She stepped back with a flush and said, “THANK YOU!” as emphatically as she could without raising her voice. “So you see it too??? God, could those dorks be any more  _blind?”_

Eileen blinked at her, but relaxed when she realized that Charlie wasn’t mad at her for prying.

“I take it there’s more to the story?” she asked dryly.

“Yeah, well, Cas and Dean have been best buddies for so long, I don’t think either of them realized it had become something else until Dean met Benny when Cas went abroad for a year. By the time Cas came back, Dean and Benny were well and truly…  _them_. Cas has been pining ever since, but he’s such a good guy that he just…” Charlie trailed off, waving her hand vaguely.

“Let me guess, he’s the self-sacrificing kind and he stepped aside when Benny came into the picture, made sure Dean never knew he was jealous?” Eileen asked shrewdly

“Yeah, pretty much.” Charlie let out a sigh and then a short laugh. “God, I’m so relieved that’s what you wanted to talk about. For a second there, I thought you were going to ask me if Cas was single and I wasn’t sure how to break the news to you.”

Eileen blushed. “Oh, no, no. I’m… I’m interested in someone else.”

“Sam?” Charlie asked.

“It’s still too new, we barely know each other,” Eileen protested, blushing harder.

“Well, that’s what game night is for,” Charlie exclaimed.

* * *

*#*#*#*#*#*#*#*#*

* * *

The next Sunday game night was only Cas, Dean, Benny, Eileen and Sam, so Charlie broke out Settlers of Cataan. The jokes flew as soon as she did, especially from Dean about having ‘wood for sheep’ while Benny laughed uproariously and Sam rolled his eyes and scolded him.

While they played, Eileen and Cas held a silent conversation, their hands flying too fast for Charlie to get more than a gist of things.

But she had a feeling Eileen had somehow found a way to broach the topic of Dean and Benny.

Eileen was a braver girl than Charlie was. That was one hornet’s nest she’d stayed away from for as long as she’d known Dean.

Dean fumbled his drink and coughed, spluttering on the liquid and Cas instantly looked up and over at him even as Benny pounded his back.

“Dean, are you okay?” Cas asked.

“Y-yeah,” Dean coughed a few more times. “Yeah, just… down the wrong pipe. I’m fine. Uh, who’s turn was it?”

“Yours, Dean,” Sam said, sending Dean one of his epic bitchfaces. “If you were paying attention, you’d know that.”

“Yeah, yeah,” Dean coughed again, grabbing the dice and shaking them up. He rolled them into the frisbee and cursed as it rolled seven.

“Ha ha, bitches!” Charlie crowed, fanning out her cards. “I’m safe!”

“Awwww… fuck…” Dean groused, counting out his cards and then sorting which ones to toss. “Well, there goes  _my_ turn. Just go, Benny.”

And that was the beginning of Dean’s bad luck. It was weird, because Dean was normally a very good player, his strategies on point. The only times he played so badly was when something was bothering him.

With the way his eyes kept straying towards Cas and then over to Benny, Charlie slowly realized that he _was_ bothered by something. Something to do with Cas. Why now, after all these years, she wasn’t sure, but as Eileen turned to converse with Sam, Charlie noticed how downcast Cas was and resolved to hold him back when everyone left for the night.

Dean continued to play poorly for the rest of the night, poorly enough that Charlie caught Benny giving him concerned glances. Sam was too engrossed in Eileen to notice anything out of the ordinary and Cas was looking like it was all he could do to keep up the façade of enjoying the time.

With all that going on, Charlie wasn’t the least bit surprised that she won the game. Nobody was in thee mood to play much afterwards and the party broke up quicker than usual.

Catching Cas’s arm before he could grab his trenchcoat, Charlie managed to hold him back after everyone else left. He looked resigned, like he knew exactly what she wanted to talk about. Taking a deep breath, Charlie dove headfirst into the Dean, Benny and Cas situation she’d always sworn to stay out of.

“Hey,” she said gently. “You’re in love with Dean, aren’t you? And Benny too?”

He sighed forlornly, looking down, the nodded without a word, like words were too much for him right now.

“Cas – why don’t you say anything? You know Poly is a thing…” Charlie offered. “And I kinda think Dean would go for that.”

“It doesn’t matter if he would or not, Benny hates me, and I won’t get in between them,” Cas said roughly.

“No, I’m sure he doesn’t hate you,” Charlie said, her eyes wide and her mind racing.

Cas shook his head, pulling away from her. “I’m used to it. Anyway, don’t worry about me. I’ll live…”

She stared after him as he left, feeling like her heart had broken all over again.

* * *

*#*#*#*#*#*#*#*#*

* * *

Game nights continued, Spring well underway and if Dean, Cas and Benny were a lost cause, Charlie took solace in the success of Sam and Eileen. The two of them more often than not sat together and conversed, Sam’s signing improving with every session.

Sam cornered Charlie during one of the game nights while helping her retrieve drinks for everyone.

“Thank you, for introducing us to Eileen. She’s a wonderful person and I think she fits in really well around here,” Sam said softly.

Charlie turned to him and beamed.

“Yeah, she really does, doesn’t she,” she said. “So uh, anything you wanna say?”

“Um, no?” Sam stared at her like a deer in headlights. She put her hands on her hips and stared him down. He squeaked and ran a hand through his hair. It was adorable how awkward and adolescent Sam could look, even in his 30’s, despite towering over her. “Okay, um… don’t tell Dean cause I don’t want him to tease me, in case she says no, but um, I’ve been thinking of asking her out.”

“Awwwwww….” Charlie clapped her hands together, and leaned in close to Sam. “That’s so sweet, Sam! Don’t you worry. I have a good feeling she’s gonna say yes.”

“You really think so?” he asked, a hopeful smile on his face.

She rolled her eyes.

“Uh, _duh_ ,” she said, slapping his chest with the back of her hand. “The Queen is _never_ wrong.”

Except when she was, she thought sadly, thinking of Gilda, of Cas. She shook her head to get rid of those thoughts.

* * *

*#*#*#*#*#*#*#*#*

* * *

Spring had given way to summer and Sam and Eileen had started dating, finally, while Charlie was no closer to figuring out a way to help Cas. He’d missed the last several sessions and she was really starting to get worried about him.

If she wasn’t mistaken, so was Dean.

Benny was hard to read, but she thought he was too.

Then Jo stormed in early, the first to arrive for game night by _hours_ , and Charlie didn’t have much time to worry about anyone else before the night started.

“Yo!” Charlie called out in surprise as the door slammed shut behind Jo, who’d barged in without even bothering to knock. “Hey Jo! What’s up?” Charlie asked.

Jo threw herself down on the couch.

“Frickin’ _mom_ ,” she grumbled. “Like I can’t be my own person. She’s always after me for something.”

Charlie sat down next to Jo and patted her knee sympathetically. “Hey, she’s just worried about you. It’s what mom’s do. You probably just need some space.”

“How do you mean?” Jo looked up sharply. “Stop talking to my mom?”

“No, no, nothing so drastic,” Charlie rushed to reassure her. “I just mean… you help her run the Roadhouse, and you both live there, so its not like you get much time to yourself, right?”

“Yeah, but… what can I do about that?”

Charlie hummed thoughtfully and her mind wandered over various ideas until it stalled out on the empty room just down the hall from where they sat.

“What if… you moved in here?” she asked slowly. Her eyes went wide excitedly.  “Yeah! Yeah, that’s a great idea! You and Mister Picklebottom get along, I have the space and you need some. It’s _perfect!”_

Jo blinked back at her before a wide but nervous grin spread over her face. “Really?”

“Of course!” Charlie said. “I wouldn’t offer if I didn’t mean it.”

Jo launched herself across the couch and pulled Charlie into a hug. “Thank you, thank you, thank you!”

For some reason, Charlie found herself blushing hotly with an armful of Jo. “Of- of course. It’s not a problem, Jo-jo.”

* * *

*#*#*#*#*#*#*#*#*

* * *

Jo was moved in faster than you could say Queen of Moondor, with Ellen making a terrifying visit one Sunday to ‘deem the place acceptable’ before agreeing that maybe Charlie made some sense about needing some space.

The move happened over the week, and they were all more or less settled in before the next game day. Despite everyone in the gaming group and then some helping Jo move her few things, that Sunday, game was supplanted by a housewarming party.

Plenty of beer and chips and tacos abounded, while Benny attempted – once more – to make friends with Mister Picklebottom (through the use of bribery, no less. Which, traitor that she was, seemed to be working).

Charlie beamed about the apartment, at how low lively and full it was. Having Jo move in was the best decision ever and she was amazed that she hadn’t thought of it sooner.

* * *

*#*#*#*#*#*#*#*#*

* * *

“I think Cas is avoiding me,” Dean said without preamble, dropping onto the couch. It was late summer, just about ready to bleed into fall, and he’d arrived alone, without Benny and hadn’t said a word when Charlie had let him in.

She’d recognized the look on his face, even if she didn’t know the cause, and she’d just chattered as gleefully and cheerfully as she could, knowing he’d open up when he felt ready, and the fact that he was here, early, on a game night, meant that he was just about ready to pop.

She was just glad Jo was out grabbing a few last-minute things for game night, or Dean would have clammed up in an instant.

Charlie was returning from the kitchen with a couple of beers when he’d finally spoken and she froze in place.

“Uh…. W-why… why would you think that?” She stuttered, forcing her feet to move again and joining him on the couch. She managed, just barely, to hold in the nervous laugh.

Cas, though. She should have _known_ it was about Cas.

Dean leaned forward on the couch, hunched in on himself, his hands clasped together and twisting about. He licked his lips and looked up at her.

“You can’t tell me you haven’t seen it? How many game nights has he missed the past few months? Way too many. It’s not like Cas. Not… not like the _old_ Cas anyway. But ever since… ever since he came back from traveling abroad – “

_Ever since you started dating Benny_ , Charlie thought sadly. How could Dean not _see_ it?

“-ever since then he’s… we used to do _everything_ together. And I get that our lives are different now, but he’s still my best friend ever – Sorry, Charlie – “

“Hey, I knew the score when we met, Deano. I ain’t mad,” Charlie said. Of course, she couldn’t rate higher than Cas because Cas was _more_ than just a best friend. So yeah, she was cool with it. Dean might not realize it but she knew the _real_ score.

“Right, right but… but we just don’t see each other as often as we used to. It’s sad how I _count_ on our Sunday games to see Cas at least once a week, but it’s like, nowadays he periodically goes into hiding. It’s not… not like him,” Dean said softly, biting at his lip. “And now… not even those…”

Charlie touched his arm and handed him the cold beer. “Do you have any, uh…. Ideas as to _why_ he might be avoiding you?”

_Please don’t be an oblivious idiot, please, please, please_.

Dean swallowed and looked away. “I… I _think_ he… he has feelings for me. And um… I might have them back.” He looked up at her intently and rushed to add, “But I ain’t cheatin’ on Benny, promise. I love him too. It’s just…”

“It’s just that you love _both_ of them, don’t you?” Charlie said, moving closer to Dean and bumping shoulders with him. “Have you talked to Benny about it?”

“Yeah, yeah,” Dean shook his head with a chuckle. “Fucker said he knew already.”

“And he’s not mad?” Charlie said, hope fluttering in her chest.

“I guess not? He trusts me. But what do I do? I miss Cas and if he’s avoiding me because of our feelings for each other… Charlie, he’s gotta be hurting. At least I got Benny, but Cas has got _no_ one.” Tears filled Dean’s eyes and Charlie melted, wrapping her arms around him.

“Oh, Dean,” she said softly.

“How do I fix this?” Dean asked, his voice rough as he buried his face in her shoulders.

Patting her shoulders, she thought back a few months, to the suggestion she’d given Cas. Slowly, she spoke. “Dean… have you heard of Polyamory?”

He raised his head. “Uh… what?”

“Polamory. Multiple partners.”

Dean shoved to his feet and glared. “I told you, I’m not cheating!”

“It’s not cheating if everyone’s on board and involved.” She leapt to her feet.

“Huh?” he blinked.

“Listen to me, you idiot. He loves you and you love him, right?”

Dean nodded slowly.

“And you love Benny?”

He nodded again.

“Well, I think Cas loves – or could easily love – Benny too.”

Dean’s eyes went wide. “Uh….”

“And Benny doesn’t seem to mind or care that you love Cas… what if…?” Charlie trailed off.

“You mean, like, the three of us. Together? At the same time?” Dean asked, his face contorted as he thought the idea through. She stayed silent, holding her breath. “Huh. I never… never considered that.”

He put the untouched beer down on the coffee table. “I gotta go.”

* * *

*#*#*#*#*#*#*#*#*

* * *

 It was midfall when Garth proposed to Bess over a game of Middle Earth Risk. Everyone had arrived that day for game night and the group was large enough that they’d divided the table into two separate games.

Everyone but Bess had known it was coming that night, though everyone _knew_ she’d been waiting anxiously for Garth to propose. She was old fashioned like that and Charlie was just gleeful she’d gotten to witness it first hand.

Garth had sleight of handed the One Ring with the engagement ring he’d picked out a while back with Charlie’s help, and with a flourish, he’d gotten down on one knee to make his speech just as he was about to win the game.

“I’d gladly give up my victory to you if you would wear my ring. Bess, you are the true conqueror here, having completely won my heart and soul the day we met. Please marry me?”

It was cheesy and so totally Garth, and Charlie might have cried some tears when Bess leapt up, launched herself at Garth and squealed “YES!” so loudly, that it pierced a few eardrums.

Sam and Eileen watched it all shyly, their hands linked together. Sam turned and he and Eileen exchanged adoring looks and Charlie was certain there’d be another proposal within the next year.

That left her, Cas and Jo as the odd men out as everyone else in their friends’ group had coupled off.

Game night dissolved into an impromptu engagement party after that, with both Jesse and Cesar, and Dean and Benny, offering up married advice.

Charlie watched Cas’s face fall as he struggled to maintain his composure and her heart wrenched. Had Dean really been against the idea she’d had? Or maybe she’d been wrong about Benny after all?

“Charlie, what’s wrong?” Jo asked, placing a hand on Charlies arm.

Charlie shrugged, looked around carefully and spoke quietly. “Uh… can’t talk about it right now, okay?”

“Yeah, sure. But you know I’m always here for you, right?” Jo asked earnestly.

Charlie smiled at Jo. “Of course. You’re one of the best friends I’ve ever had.”

Jo smiled back but it was tinged with something sad, resigned. A lot like Cas’s smiles had been of late, as a matter of fact. Charlie stared after Jo as she walked away and mulled it over.

Cas was the first to try and leave as the party started breaking up, and Charlie felt hope wash over her when she saw Dean grab Benny and whisper something and Benny pushed him off towards Cas.

Maybe Dean _had_ taken her advice, but for whatever reason, hadn’t been able to implement it.

* * *

*#*#*#*#*#*#*#*#*

* * *

“I can’t believe it’s _snowing_ already,” Jo complained as she stomped into the apartment with a couple of grocery bags. She was covered in snow and hadn’t even been wearing a hat or mittens and Charlie bounded over the apartment to rescue Jo. She pulled the bags out of her arms to place on the table and then grabbed Jo’s fingers.

“God, you’re freezing, Jo!”

Charlie pulled Jo’s hands up and rubbed at them, then breathed on them hotly, Jo making a strange noise when she did.

“I just hope this doesn’t cancel our game night. I’ve been looking forward to it,” Jo managed to groan out as Charlie continued to rub at her hand. Finally, pink cheeked, Jo pulled away. “I’m gonna go take a shower and warm up.”

Charlie let go, turning red for some strange reason as she did. “Ah! Right. You go… do that…” Why was she blushing?

Turning quickly as Jo left the room, Charlie picked the bags off the table and brought them into the kitchen to sort them, reflecting on how things had changed since Jo had moved in. For one, Jo was a stubborn ass, but so was Charlie, sometimes. They had a lot of things in common – game night and friends – but plenty of other things they didn’t, which landed them plenty to talk about. Jo was also passionately loyal to her friend and family and always doing little things around the house that Charlie didn’t always catch on to right away, but when she did…

She was hella grateful.

But did she ever _tell_ Jo that?

Charlie put away the drinks and grabbed a couple of bowls for the chips and nibbled at her lips as she filled them up and brought them to the table. She needed to do something to show Jo her appreciation, that was for sure. That she didn’t take Jo for granted. Jo livened up the little apartment greatly and Charlie was really damn grateful, every day, that Jo had moved in.

Jo emerged from the shower, toweling off her long hair with a hum and walking through the apartment barefoot. Charlie almost dropped the chips.

What was _wrong_ with her?

A knock at the door interrupted her thoughts and she gratefully spun away to answer it and let the first of the gaming night guests in.

* * *

*#*#*#*#*#*#*#*#*

* * *

Charlie stomped her feet on the mat outside of her apartment. Winter had well and truly settled in, and the snow was everywhere but she didn’t need to be tracking it in and making a damn mess of everything.

Especially with all their friend due to arrive any second now. Thankfully, Jo was able to man the store while Charlie went out for a few, last minute things.

And accidentally found the perfect cheer Jo up card. She’d been looking a little down in the dumps lately and Charlie was afraid Jo regretted moving away from home. The idea that Jo might leave squeezed Charlie’s heart and had her fearfully thinking of any way to convince Jo to stay.

Of course, if Jo would rather leave, Charlie wouldn’t stop her, but…

The door opened under her hand and Charlie tumbled inside, kicking off her shoes by the door. Jo wasn’t alone, she noticed, but Dean, Cas and Benny were all there too.

“Hey, you guys are early,” Charlie said, grinning. Then she took in the way they were sitting, how closely they were sitting on her couch, Cas in the middle, and blinked. “Did you all come together?”

“Uh, yeah, we did,” Dean said. He rubbed at the back of his head sheepishly. “Actually, we had something to tell you, and we wanted to do it before everyone else got here cause I just _know_ you’re gonna make a big deal of it.”

Charlie paused on her way to dropping the bags off in the kitchen and stared at them. the meaning of Dean’s words ticked over and she squealed, dropping the bags for real, right there on the floor, before launching herself across the room.

“Really?” she asked, breathlessly. “All of you, right? I was right?”

Dean blushed and Benny laughed.

“Yes, Charlie, you were right,” Cas said, his smile happier than any she’d seen from him in _months_.

“Oh no,” Dean groaned. “Don’t you say that! Now she’s gonna lord it over us for the rest of our lives.”

Cas looked between Dean and Benny, grabbing each of their hands in his. “I think I can live with that.”

“Awwwww…” Charlie melted at the sight of the three of them. “So I’m the first to know?”

Jo cleared her throat and Charlie looked over to see her bending over to pick up the bags. Remembering the card inside one of the bags, Charlie panicked. “Wait! Don’t touch those!”

Blinking, Jo dropped the bags. “Suit yourself.”

She stalked off to her room and the slamming door had Charlie wincing.

“What was _that_ about?” Dean asked, getting up off the couch.

“I don’t know!” Charlie wailed. “I think Jo wants to move out. She’s kinda been in a bad mood lately.” Charlie sniffled and she wiped at her eyes. “But I don’t want her to go. And I got her something at the store to cheer her up but I didn’t want her to find it before it was ready and… and…”

Arms wrapped around her as Dean pulled her close to him in a warm, comforting hug. He patted her on the back as she tried to stop crying. Why was she being so emotional about this? Jo moving out didn’t mean they weren’t still friends or anything, right?

“But why do you think she wants to leave?” Cas asked, head tilting. “How does a bad mood equate moving out?”

“Gilda moved out,” Charlie said, mumbling the words into Dean’s shirt.

Dean’s hand paused a second and then he chuckled before resuming the comforting motion. Charlie pulled back and glared at him.

“You think this is a laughing matter?”

He shook his head, but his mouth was twitching into a smile. She punched his arm. “Dude! I’m being serious here!”

“Charlie… why were you upset when Gilda moved out?” Dean asked softly.

“Wha – that… that was different,” she said with a squeak.

“Are ya sure, darlin’?” Benny asked, just as gently as Dean.

“I…” Charlie floundered, her eyes going wide with a gasp. “Oh my god…” she breathed out.

“Why don’t we get out of your way for the night?” Cas asked. “We can call everyone and let them know to reschedule, if you’d like to talk to Jo with some privacy.”

“Um, right, yeah,” Charlie said dazedly, her mind whirling. “Sounds good.”

Dean let go of her, Benny and Cas getting up from the couch. They hugged her, Cas wishing her good luck, before the three of them found their shoes, grabbed their coats and left.

Leaving Charlie standing there alone with her sudden realization.

She was in love with Jo.

When it had happened, she didn’t know, but it was true. And maybe… maybe Jo could, maybe, like her back?

Wait, how did she know that? Dean hadn’t said anything like that, nor had Benny or Cas. As far as she knew, Jo had never dated girls, so why was she suddenly so convinced? Jo’s suddenly surly behavior didn’t necessarily mean that she was getting frustrated with Charlie’s obliviousness. There could be any number of reasons for her behavior.

But then, would Dean, Cas and Benny have so easily suggested she talk to Jo after finally realizing her feelings? What if they knew something? What if Jo had talked to them about Charlie? What if Charlie stood a chance at all?

And that, she realized, was what had her so convinced that Jo liked her too.

Maybe.

Charlie swallowed, looking over at the bags, then at Jo’s door. Coming to a decision, she strode back to the bags and picked them up, scrounging around inside for what she’d found.

The card came out first and she fished out a pen, quickly writing inside of it, putting it in the envelope and closing it. Then the box of chocolates and from a different bag, a couple of Jo’s favorite flowers.

Freaking chocolates.

And flowers.

How had she not realized?

Quickly arranging all the little gifts, Charlie stood in front of Jo’s door and… panicked. She put everything on the floor, knocked and ran to her room, shutting her door behind her.

She slid against the door till her ass hit the floor and held her breath, listening carefully.

Jo’s door creaked open.

There was a couple of muttered words before a surprised gasp. Then silence. There was no way Charlie could hear her opening the card through the door and halfway down the hall, but she could imagine it in her head…

Jo looking left then right and getting pissed that someone had knocked and run, then looking down by accident to see the gifts. Confused, she went for the card first and opened it – and that’s where Charlies imagination failed her, unable to be entirely certain Jo would react positively and unwilling to imagine Jo reacting negatively.

Her heart pounded and she didn’t hear the footsteps that must have made their way up the hall because she almost jumped when there was knocking at her door.

“Charlie, you ass, get out here,” Jo called through the door.

Swallowing, Charlie stood and turned and opened the door just enough to peek through the crack, trying to assess the situation.

“Seriously?” Jo said, holding up the card.

Charlie stared at the simple white card with the smiley face on it that said, in very bold letters, ‘I hope your day is as nice as your butt’. It had been meant to be funny, but now all she could see was how offensive it was.

“I’m sorry,” Charlie whispered, her heart breaking over how much worse she’d just made things.

“Sorry for what? For being oblivious for the last two years? I thought finally moving in would give me the edge I needed to let you know I was interested in you and it took you freaking forever to just… _notice_ me,” Jo said plaintively.

Charlie perked up and opened the door a little wider. “Wait, so you’re not mad about the card?”

Jo snorted. “I’m mad that it took you so long to notice. The card is funny, and the inside is super sweet. No, I’m not moving out, not as long as you want me to stay, actually, truly stay. You just asked me out, Charles, you can’t get rid of me _that_ easy,” Jo said, grinning widely.

“Oh thank god,” Charlie heaved out in relief, flinging the door wide open and pouncing on Jo, pulling her into a bone crushing hug. “I’m so sorry I was an idiot.”

“Don’t be sorry,” Jo said softly, mirth in her voice. “Help me make up for lost time?”

Their lips met in a kiss, so unlike any other Charlie had ever had, and with each passing moment they held each other close, winter got just that much warmer.

 

 

**Author's Note:**

> Tagging the couples and characters for this was tough because i normally do a Major/minor tagging but the story is so short that nobody is really that minor, but I hope that nobody's disappointed by how much time each character gets compared to others. it just... happened like that.
> 
> but i thought it would be particularly funny if Charlie spent all that time matchmaking and not even realizing her match was right under her nose.
> 
> Remember that anyone can participate in a [ ReversePrompt Challenge ](https://reverseprompts.tumblr.com/)\- at any time! Be sure to add it to the collection and tag the tumblr so we don't miss it. Even if a new challenge is started, you can do an old one if you want - there's no deadlines. We are trying to keep all art prompts as open fandom as possible so anyone can write anything but we acknowledge that depending on our artists, that might not be doable.
> 
> And if you have any suggestions for our artists, send them through ;D
> 
> THanks!


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